I would say this about itachi since he's my favorite ninja along with hashirama....his weakness is stamina basically, if he doesnt finish a fight quickly, then most likely he'll lose.

you forgot to mention the time where sage kabuto just cut itachi in half outta frustration...

It's tricky to say who woulda won, on one side you have itachi who is one of the most powerful ninja in the series on Naruto...with basically is only weakness being stamina, and the other side you have 3rd raikage, who basically can take a hit from a rasenshuriken from a KCM naruto and still get up like it was nothing, remember when madara absorbed his rasenshuriken then stated "too much energy" meaning he didnt absorb all of it, for raikage to take that hit, means he's hella tanky, and i think i seen someone that 3rd raikage is faster than 4th raikage, remember this is a guy who fought thousands of ninjas in one night i think, as stated in the manga i believe, so it would be a battle either of endurance or wits, it would be hard to tell who woulda won, solely based on what they can do or what they've achieved, we know more about itachi than 3rd raikage.

ofc itachi strongest weapon imo is his wits...he's one of the if not the best *yzer in a battlefield, and ofc the battle experience he carries, is a plus, kabuto barely had that compared to him, so itachi knew how to fight and how to approach hard situations, similar to kaguya vs naruto and sasuke, she had the power, but lacked the experience to fight properly.